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. 2013 Sep 16;18(9):11485-95.
doi: 10.3390/molecules180911485.

Fremy's salt-mediated oxidative addition. A new approach in the total synthesis of naturally dipetalolactone and its immunomodulatory activity

Yasser Selim  1 , Nabil Ouf, Mohamed Sakran
Affiliations

Fremy's salt-mediated oxidative addition. A new approach in the total synthesis of naturally dipetalolactone and its immunomodulatory activity

Yasser Selim et al. Molecules. .

Abstract

The structure of the natural dipyranocoumarin dipetalolactone has been confirmed by an unambiguous synthetic route from resorcinol. This sequence was initiated by a pyran ring formation step which introduced the 3-chloro-3-methylbut-1-yne moiety. Then, the expected product undergoes a Fremy's salt-meditated oxidative addition followed by ring closure to yield dipetalolactone. Dipetalolactone was also found to have immunological activity in a mouse carcinoma S180-bearing mice cell line.

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Figures

Scheme 1
Scheme 1
Total synthesis of natural dipetalolactone.
See this image and copyright information in PMC

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